Synthetic approaches to actinobolin and actinobolamine, the hydrolysis product of the chemotherapeutic agent actinobolin, a broad spectrum antibiotic of proven effectiveness against certain types of neoplastic diseases have been devised. In the synthesis of actionobolamine advantage is taken of a rearrangement of readily available dehydroisoquinuclidines discovered in our laboratories. The importance of actinobolin and actinobolamine as synthetic goals are: (1) structural and stereochemical isomers of these molecules can be generated, (2) intermediates in the synthesis of actinobolamine are of derivative concern in studies directed toward the synthesis of anti-tumor agents similar to the Vinca alkaloids vinblastine and vincristine, (3) a better understanding of interactions between nonbonded atoms and of mechanistic aspects of organic reactions in azabicyclic structures will be realized.